CHEM 760/7600 - Heteroatoms in Organic Synthesis

Semester: Fall 2022

Professor: A. Schwan | Discipline: Organic | Campus: Guelph

Description

The course is intended to provide students with an understanding of the utility and mechanism of heteroatom-based functionalities in organic synthesis.  The influence of the heteroatom will be emphasized with examples displaying how the heteroatom directs reactivity and where applicable, stereochemistry. Students will be required to deliver two seminars and write two research essays which, when totaled, will comprise a major component of their grade.

Method of Presentation: One 2 1/2 hour lecture per week, Wednesday nights starting at 7:00 pm on TEAMS. First lecture is Wed. Sept. 14, 2022.  The scheduled lectures will be composed of Schwan lecturing for 7 class periods and 4 class periods of student presentations.

Schwan lectures will introduce functional groups and their bonding and electronic characteristics and also will survey the families of reactions applicable to the functional groups. Presentations by the students will provide a more in-depth assessment of particular reactions or groups of reactions based on the heteroatom functional group.

Learning Objectives

-to recognize and understand the role of key heteroatom containing functional groups in organic synthesis
-to communicate synthetic and mechanistic chemistry brought about by heteroatom containing functional groups
-to compile and summarize a finite aspect of synethic chemistry
-to increase the student’s synthetic chemistry knowledge by unveiling new and valuable  functional groups and reactivity modes
-to grow a students mechanistic skills by broadening their exposure to a wider selection of chemistries and reactive intermediates
-to develop an understanding of the role of uncommon bonding effects in organic chemistry
-assist in the development of skills for critical assessment of scientific information

Materials

Conventional sources of references:

Library including online books

SciFinder

Google Scholar

Wikipedia

Web of Knowledge

Unconventional sources of references:

http://www.organic-chemistry.org/

Science of Synthesis is available on Guelph campus (at least):

http://thieme-chemistry.com/thieme-chemistry/sos/trials/?WT.mc_id=IS_SOS_OrgChem_14-10_Product-of-the-month

www.synarchive.com

Evaluation

The course grade will be based on two oral seminars, two research essays and a final exam The final examination will be given in early December.

The final grade will be calculated as follows:

research seminar 1            15%     `                  on Oct. 12 or 19

research essay 1               20%                       due Oct. 26

research seminar 2            20%                       on Nov. 16 or 23

research essay 2               25%                       due Nov. 30

final examination               20%                       suggested to be Dec. 6

Presentations and research essays are expected to contain mechanism components, synthetic examples, selectivity features, local (geographic) connections of contributions, and demonstration of heteroatom properties to observed chemistry. Essays are expected to mirror the presentation. See additional documentation for further instructions and guidance.

Main heteroatoms to be addressed: sulfur, selenium, silicon, phosphorus, boron

Anticipated Marking Scheme (with consideration to guidelines and expectations noted above):

SEMINAR

Discussion & Engagement of others’ presentations

(quantity and quality)                                                           2
Slides                                                                           5
Oral Presentation and Clarity                                               6
Quality and Frequency of Questions Asked                           3
Scientific Content                                                              14      /30

ESSAY

English                                       5
Typos/Syntax                              5
Reference Compilation                5
Scientific Content                        15      /30

Lab/Project

General Content Components

Brief history (longer if there is an important evolution of the reaction)
Chemical methods to incorporate the heteroatom, if applicable.
Requirement of bonding features unique to the heteroatom (“This reaction works because….” or “The stereochemical outcome is due to……”)
Mechanism with modern references; any mechanism reinterpretations or contentious points?
Value in synthesis with examples:  important methodology; natural products or drugs or industrial application,  if possible
Any selectivity features of the reaction?
Any local contributions? (GWC2?, Ontario? Canada? Michigan or Upstate NY?)
Any sustainable aspects or conditions? (green achievements, atom economy, circumvent protecting groups?)
What other reactions effect similar chemistry, if any?
Have the reagents or conditions evolved over time?

Seminar:

Components as above plus :

Effective screen layout: Consistent appearance (all molecules the same size), your original graphics with no mistakes, effective atom size/bond length ratio; innocuous reaction arrows; balance of text and atom size to molecule size (ACS Document 1996 ChemDraw setting highly recommended) ; 4 to 8 molecules per slide

Good speech
10-12 minutes in length
Questions from others: At least 1 question for every two presentations

Written report:

Components as above plus :
Good flow; good, mature English; proper use of articles; self consistent reference structure and syntax; proper journal abbreviations (CASSI) – use JOC format
Absolutely no plagiarism. Text will be compared to www using “Turnitin”.
No tables of R groups/conditions/yields. Use a reference manager. Get copyright permission for inclusion of someone else’s graphics (append the email to your report).

15-20 double spaced pages including diagrams but not including references. Submitted as Word file or as pdf.

The slides you employ for your presentation are to be distributed to the class (via Schwan) before your evening presentation.

Also, presenters are expected to provide a 1 page mechanistic and synthetic summary to other classmates as a study summary for the final exam.

Timing Advice and due dates:

Week 1: claim a topic (Day 1 for this), find too many references and start learning the material
Week 2: Choose references for inclusion; start drawing molecules; start planning structure of seminar and essay.
Week 3: Bring the seminar to a point of near completion, while adding fragmented points and thoughts to your essay;
Week 4: finalize presentation and send tentative presentation to Schwan for feedback; do substantial writing of essay
Week 5:  Oct. 12, some students present
Week 6: Oct. 19,   other students present; 2nd topic decided
Week 7: Oct. 26, Essay 1 due (option to send for Turnitin assessment prior)
Week 8 work on 2nd topic, reference gathering, presentation and essay
Week 9 work on 2nd topic, reference gathering, presentation and essay
Week 10 Nov. 16, other students present
Week 11 Oct. 23, some students present
Week 12: Nov. 30, Essay 2 due  (option to send for Turnitin assessment prior)
Week of Dec. 5, final exam

Schedule

  • Wed: 7:00 pm - 9:20 pm in MacN 101

Office Hours

Office: MacN 336, Guelph Campus. 824-4120 X58781; E-mail: [email protected] FAX: 1-519-766-1499